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Compare 706 Vacation Homes in Windham with updated reviews, rates, and availability.

A beautiful ocean view cottage. Come enjoy the wonderful beach!
10.0 out of 10, Exceptional, (93)
"Perfect for a family and friends weekend! Lots of room for everyone to be comfortable!"
A beautiful ocean view cottage. Come enjoy the wonderful beach!
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)
9.6 out of 10, Exceptional, (71)
"Enjoyed this peaceful home and property. "
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (110)
"This property is exactly as it’s listed. Mr. Murphy is a kind and helpful host. The location can’t be beat. So close to anything you’d want to see and right on the beach. Watching the dogs play on the beach and the boats was a highlight. The view is so beautiful it looks fake lol. I truly hope to be back one day. "
Charming 110-year former Inn 10' from the Ocean!
Luxurious Penthouse with Modern Design in Downtown
9.0 out of 10, Wonderful, (4)
"We had everything around us. Didn’t loose a minute for commute, everything was perfect. "
Luxurious Penthouse with Modern Design in Downtown
Enchanting 3BR Farmhouse Retreat Nature Getaway
9.0 out of 10, Wonderful, (9)
"If you need a place to stay in your way to Boston or Acadia, this will work fine. It was clean and newly remodeled. The host is very quickly responsive, but unfortunately was not able to answer our questions. The house has limited cooking supplies and dishes, and wash cloths were not provided. Overall, it was fine for passing through, but not well stocked or ready for an extended stay. "
Enchanting 3BR Farmhouse Retreat Nature Getaway
East Grand Ave Fabulous Cottage
9.2 out of 10, Wonderful, (131)
"The picture on VRBO leads you to believe you just go down the pathway shown to get to the beach when you are actually in a neighborhood and have to walk down the street to get to the beach. The house was very clean and both beds were very comfortable. The host was very fast to respond to my messages. Needs clean shower liner. We enjoyed our stay. "
East Grand Ave Fabulous Cottage
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Full sized home
9.6 out of 10, Exceptional, (22)
"Short visit but fun little cottage off the beaten path. Most comfortable beds ever and very responsive host and caretaker. Would stay here again. Loved the nearby waterfront restaurants."
The price is SAR 939
SAR 1,515 total
includes taxes & fees
3 Nov 2024 - 4 Nov 2024
Full sized home
The Gregory House in Southern Maine close to many beaches & popular destinations
9.6 out of 10, Exceptional, (12)
"The Gregory House is in a great location in southern Maine. It's 30 minutes south of Portland and close to most of the south coast beach towns. All amenities you'll need are close by. The house itself is an old mansion and has tons of space. The 3rd floor has a grand, pitched ceilinged, wood paneled pool room with comfy couches and a large screen TV. Lots of games are available as well in the storage drawers there. There's also a card room in the main turret - very cool. The front porch has lots...
The price is SAR 2,441
SAR 4,208 total
includes taxes & fees
3 Nov 2024 - 4 Nov 2024
The Gregory House in Southern Maine close to many beaches & popular destinations
Oceanside escape 🌊 perfect family getaway!
9.8 out of 10, Exceptional, (10)
"Beautiful home! Well kept, clean and very comfortable. A little touch of history in this wonderful house and neighborhood. Great location, quick to Portland and the airport. We loved it!!!! Owner communication is a 10+++. "
Oceanside escape 🌊 perfect family getaway!
Sea-clusion by the sea! Cozy cottage within step of the beach!
9.4 out of 10, Exceptional, (30)
"Very nice little house. That being said, the house was good for us as we weren’t there much, but if you plan on spending a lot of time in the house it is small, the bathroom is made for small people. I would recommend this listing as the host is very quick to respond and very pleasant and helpful."
Sea-clusion by the sea! Cozy cottage within step of the beach!
Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views
10.0 out of 10, Exceptional, (3)
"House was great, location was perfect and the local property manager was very responsive and helpful. "
Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (54)
"Cute little spot near oxbow. Short drive to downtown. Great kitchen if you cook. Neighborhood seems Soso during the day and strangely decent at night. Pretty ideal. Best deal the weekend we stayed even over all the hotels. Worked out great. "
The price is SAR 612
SAR 1,585 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
Elegant condo - walk to Portland's best restaurants & Old Port
Rent a room in the gorgeous Holt House
8.2 out of 10, Very Good, (22)
"We loved staying at the Holt House. It's a truly beautiful building. It's like staying in a hotel from another era. The room was beautifully decorated with victorian decor and we loved it. It was also handy to have access to a full kitchen on the first floor where we washed some of our dishes. Overall, it was a cozy and quiet place to stay."
Rent a room in the gorgeous Holt House
Bayside House Near Portland with Water Views, Fast WiFi, & Patio - Dogs OK
8.6 out of 10, Excellent, (12)
"This is owners first year renting. It needs a complete review by electrician because there are several outlets not working. We also had trouble with the thermostats and heat. So that needs help too. The 1800 salt box portion of the home was charming to us. The addition added a great number of beds and baths. The kitchen was marginally stocked with bowls, etc so bring your own.. kitchen could have been cleaner too. So not smooth sailing but a comfy no fuss second home"
Bayside House Near Portland with Water Views, Fast WiFi, & Patio - Dogs OK
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
9.6 out of 10, Exceptional, (32)
"We loved the location and the house. There were beautiful views from the deck of the bay. It was slightly secluded. We saw a few deer right in the yard. The house was very clean and well stocked."
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
The Moonglow! A beautiful ocean view house in Biddeford!
9.8 out of 10, Exceptional, (93)
"Great location and beautiful home. Looking forward to renting out again. "
The Moonglow! A beautiful ocean view house in Biddeford!
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!
10.0 out of 10, Exceptional, (132)
"Beth’s apartment is amazing, and the location is absolutely perfect. You have complete privacy, even though the apartment is attached to her house. We will definitely be returning. Thank you, Beth!"
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!
☼ Maine Lakefront Getaway ☼
9.6 out of 10, Exceptional, (62)
"We had a lovely stay! The house was just right and the lake was beautiful "
☼ Maine Lakefront Getaway ☼
Entire House! Beach Views . Less then a 1 minute walk to the Beach.
10.0 out of 10, Exceptional, (36)
"The house was beautiful and the view of the ocean on the second floor was amazing. I would love to return again. Thank you."
Entire House! Beach Views . Less then a 1 minute walk to the Beach.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Windham

Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
8.4 out of 10, Very Good, (32)
"We would absolutely book this house again. Super peaceful location. Loons in the morning were a stellar start to each day. "
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (95)
"This beach home was clean and beautiful, it had everything we needed and was in a great location. We loved that it was right on the ocean, which meant amazing sun rises and easy access to walks on the beach. We were there in October, so there wasn’t much going on in Old Orchard beach, but that was okay with us! It was a quiet cozy town when we were there. There were plenty of other places to visit in the surrounding area!"
Gorgeous ocean-front home with stunning beach views
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (89)
"We really enjoyed our stay. This little third floor walk up was a perfect place for my husband and I to explore Portland. It is homey and comfortable and spotless. If you have any issues with mobility you should look elsewhere, but that is disclosed in the listing. The last set of stairs are very steep, but we found it charming. I highly recommend this rental. Well done! "
The price is SAR 417
SAR 778 total
includes taxes & fees
6 Nov 2024 - 7 Nov 2024
Adorable Portland getaway on the Eastern Promenade
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.